Yellow azo dye.



KARL F-IAGEMANN, OF LEVERKUSEN,

'II-IETIC PATENTS 00., INCL, OF NEW NEAR COLOGNE, GERMANY, ASSIGNOR TOSYN- YORK, N. Y., A CORPORATION OF NEW YORK.

.YntLow AZO DYE.

No Drawing.

To all whom it may concern Be it known that I, lKARL HAGEMANN, doctor ofphilosophy, chemist, citizen of the German Empire, residing atLeverlmsen, near Cologne-onthe-Rhine, Germany, have invented new anduseful Improvements in Yellow rizo a specification.

I have found that new and valuable azo dyes can be obtained by combiningthe diazo compounds of amino-acidyl derivatives of ortl1oaminophenolsulfonic acids, such as pa ra-aminotoluolsulfonyl-2-amino4- or 6-)chlorophenol-6(or 4-)sulfonic acid, metaaminobenzoyl 2- amino 4 (or 6)chlorophenol-fi-(or 4-)sulfonic acid, para-aminobenzoyl 2 amino- 6 (or4:")6111010131161'101' l or 6-)sulfonic acid, meta-aminobenzoyl-2-aminophen0l4-sulf0nic acid, with a methylketol.

The new dyes dye chrome mordanted wool pure yellow shades. Mordantcolors produced from ortho-aminophenol derivatives with components haveoften been described. But all these colors though they dye yellow shadesdirect on the woolen fiber, change considerably in shade on beingaftertreated with bichrome, the change being from an orange to the redor blue-red side, according to the color used. stuffs, the new productsalter but very little when aftertreated with bichroine. They give pureyellow shades distinguished by great clearness, fastness to milling andexcellent fastness to light. The new dyes are after being dried andpulverized in the shape of their alkalin salts reddish-brown toyellowish powders soluble in water, caustic soda lye and concentratedsulfuric acid, generally with a yellowish coloration. They yield uponreduction with acetic acid and zinc powder an aminoacidyl compound of anortho-aminophenol sulfonic acid and a 3-aminomethylketol compound.

Yellowish to pure yellow chrome lakes very fast to light and fast tomilling can be produced on the fiber with the new color ing matters.

In order to illustrate the new process more fully the following exampleis given, the parts being by weight :84.3 parts of para aminobenzoylortho aminophenol Dye, of which the following is Specification ofLetters Patent. Application filed April 21, 1914.

l j I 'tion of Contrary to these dye- Patented Oct. 27, rate. Serial No.833,469.

para-chloro-ortho-sulfonic acid are dissolved in 1000 parts of Water anddiazotized with 42 chloric acid (195 Be.) sodium nitrite.

obtained is then of 14.5

parts of hydroand 6.9 parts of The diazo compound thus stirred into acold solution parts of methylketol with the addi- 69 parts ofhydrochloric acid. After stirring the copulation is soon complete andthe dyestufl is salted out, filtered 03 and mixed with sodium carbonate.It is after being dried and pulverized in the shape of its sodium salt acanary-yellow powder soluble in water and concentrated sulfuric acidwith a yellowish coloration ing upon reduction with zinc powder andacetic acid para-aminobenzoyl-2-amino-4- chloro-l-phenol-G-sulfonic acidand 3-aminomethylketol. It has in a free state most probably theformula: on so3n 1 i\H-co l 1' 5 4 3 I2 a" 01 \l/ M l l l CH? 7 Whenprinted with acetate of chromium on the fiber a pure yellow shade isobtained very fast to light and fast to milling.

I claim 1. The herein described new azo dyestuffs being derived from anaminoacidyl compound of an ortho-aminophenol sulfonic acid and amethylketol compound, which are after being dried and pulverized in theshape of their alkalin salts reddish-brown to yellowish powders soluble.in water, caustic soda lye and concentrated sulfuric acid generallywith a yellowish coloration; yielding upon reduction with acetic acidand zinc and yield and 53 parts of soda powder an aminoacidyl compoundof an orthoaminophenol sulfonic acid and a 3- aminomethylketol compoundfurnishing'on the fiber yellowish to pure yellow chrome lakes fast tolight and to milling, substantially as described.

2. The herein described new azo dyestufi' having, in a free state mostprobably the which is after being dried and pulverized in in the shapeof its sodium salt a canary- Gopies of this patent may be obtained forfive cents each, by addressing the Washington, .D. 0.

witnesses.

KARL HAGEMANN. Witnesses:

Louis VANnonN, HANS BRI'iKNER.

Commissioner of Patents,

